A NOVEL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF MANZAMINE-A - CONSTRUCTION OF THE TETRACYCLIC ABCE RING-SYSTEM

被引:107
作者
MARTIN, SF
LIAO, YS
WONG, YL
REIN, T
机构
[1] Department of Chemistry and Biochemistry, The University of Texas, Austin
关键词
D O I
10.1016/S0040-4039(00)75792-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantiomerically pure tetracyclic ABCE subunit of manzamine A has been constructed by an intramolecular Diels-Alder reaction of the vinylogous imide 13 to give the ABC tricyclic core 14; elaboration of 14 into 16 followed by a novel olefin metathesis reaction to form the azocine ring then delivered the tetracycle 17.
引用
收藏
页码:691 / 694
页数:4
相关论文
共 29 条
[1]   STEREOCONTROL IN THE INTRAMOLECULAR DIELS-ALDER REACTION .3. A POTENTIALLY GENERAL-METHOD FOR THE SYNTHESIS OF CIS-HYDRINDENES BY USE OF (Z)-DIENE UNITS [J].
BOECKMAN, RK ;
ALESSI, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (11) :3216-3217
[2]   SYNTHESIS OF THE TRICYCLIC HEART OF MANZAMINES [J].
BRANDS, KMJ ;
PANDIT, UK .
TETRAHEDRON LETTERS, 1989, 30 (11) :1423-1426
[3]  
BRANDS KMJ, 1990, HETEROCYCLES, V30, P257
[4]   SYNTHESIS OF THE HOMOCHIRAL TRICYCLIC HEART OF MANZAMINE-A [J].
BRANDS, KMJ ;
MEEKEL, AAP ;
PANDIT, UK .
TETRAHEDRON, 1991, 47 (10-11) :2005-2026
[5]  
GRUBBS RH, 1992, J AM CHEM SOC, V114, P7324
[6]   SYNTHESIS OF THE PYRROLO[2,3-I]ISOQUINOLINE SUBSTRUCTURE OF THE MANZAMINE FAMILY OF ALKALOIDS [J].
HART, DJ ;
MCKINNEY, JA .
TETRAHEDRON LETTERS, 1989, 30 (20) :2611-2614
[7]  
HART DJ, 1992, TETRAHEDRON LETT, V33, P6247
[8]   A STUDY OF INTRAMOLECULAR DIELS-ALDER REACTION [J].
HOUSE, HO ;
CRONIN, TH .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (04) :1061-&
[9]   NEW MANZAMINE ALKALOIDS FROM A SPONGE OF THE GENUS XESTOSPONGIA [J].
ICHIBA, T ;
SAKAI, R ;
KOHMOTO, S ;
SAUCY, G ;
HIGA, T .
TETRAHEDRON LETTERS, 1988, 29 (25) :3083-3086
[10]  
IMBROISI DD, 1989, TETRAHEDRON LETT, V30, P4309